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Volume 69 
Part 7 
Page o1074  
July 2013  

Received 5 June 2013
Accepted 5 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.005 Å
R = 0.086
wR = 0.250
Data-to-parameter ratio = 13.8
Details
Open access

3-(Prop-2-yn-1-yloxy)phthalonitrile

aFaculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C11H6N2O {systematic name: 3-(prop-2-yn-1-yloxy)benzene-1,2-dicarbonitrile}, the 14 non-H atoms are approximately coplanar (r.m.s. deviation = 0.051 Å) with the terminal ethyne group being syn with the adjacent cyano residue. In the crystal, centrosymmetric dimers are connected by pairs of C-H...N interactions and these are linked into a supramolecular tape parallel to (1-30) via C-H...N interactions involving the same N atom as acceptor.

Related literature

For background to functionalized phthalocyanines, see: Chin et al. (2012[Chin, Y. J., Tan, A. L., Wimmer, F. L., Mirza, A. H., Young, D. J., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2293-o2294.]). For background to the synthesis of precursor nitriles, see: Wu et al. (1998[Wu, Y., Tian, H., Chen, K., Liu, Y. & Zhu, D. (1998). Dyes Pigments, 37, 317-325.]); Seven et al. (2009[Seven, O., Dindar, B. & Gultekin, B. (2009). Turk. J. Chem. 33, 123-134.]).

[Scheme 1]

Experimental

Crystal data
  • C11H6N2O

  • Mr = 182.18

  • Monoclinic, P 21 /n

  • a = 4.014 (4) Å

  • b = 6.833 (7) Å

  • c = 33.85 (3) Å

  • [beta] = 90.77 (2)°

  • V = 928.1 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 153 K

  • 0.30 × 0.16 × 0.08 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.993

  • 6610 measured reflections

  • 1751 independent reflections

  • 1310 reflections with I > 2[sigma](I)

  • Rint = 0.071

Refinement
  • R[F2 > 2[sigma](F2)] = 0.086

  • wR(F2) = 0.250

  • S = 1.13

  • 1751 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...N1i 0.95 2.47 3.335 (6) 151
C9-H9...N1ii 0.95 2.51 3.402 (6) 156
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5321 ).


Acknowledgements

We gratefully acknowledge Dr Zhang Wen-Hua, Institute of Materials Research and Engineering, Agency for Science, Technology and Research, Singapore, for the X-ray data collection. We also gratefully acknowledge funding from the Brunei Research Council (UBD/GSR/S&T/17), and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR-MOHE/SC/03).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chin, Y. J., Tan, A. L., Wimmer, F. L., Mirza, A. H., Young, D. J., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2293-o2294.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Seven, O., Dindar, B. & Gultekin, B. (2009). Turk. J. Chem. 33, 123-134.  [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wu, Y., Tian, H., Chen, K., Liu, Y. & Zhu, D. (1998). Dyes Pigments, 37, 317-325.  [ChemPort]


Acta Cryst (2013). E69, o1074  [ doi:10.1107/S1600536813015663 ]

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